I have successfully implemented the recommendation pipeline, and have worked with my piano school to incorporate the results into the next month's recital. We will see how that goes.
As for the list of candidate songs, that was a difficult part. It turns out the Billboard hits of the day did not include some of the most iconic songs, and some of the top songs nobody knows about today.
However, I did come across a list of the most requested songs of the 50s and 60s, and used that for my candidate songs.